I didn't want to slag on anyone's picks in my commentary, but the biggest stunner to me was actually Dogma in the first round. I love Dogma, think it's an underrated satire, and would have happily picked it... in round 3.

Your roster is damn strong. I don't care for Chasing Amy, but it was a no-brainer pick at that point. The only reason I shied away from Saving Private Ryan and True Grit is that I don't think of those as "Matt Damon movies"... and even then, I'd grab True Grit over Contagion if I could do it over again.

If I lose this with the best War film ever made...A Coen Bros Western...A Kevin Smith classic...The highest reviewed and grossing Bourne film...A top ten romantic of the decade...AND GOOD WILL FRIGGIN' HUNTING!!!!....I will just retire from drafting because I don't know anything.

I think it makes more sense than you give it credit for. I'm not gonna go pick by pick, but I think the general thinking was to get (good) films that prominently featured one or both of them first. And sure - Damon might be 4th or 5th-most prominent in O11, but it's still an ensemble and there are still good films that star one or the other that went first. If it was "just take the best movie!," something like Private Ryan would go first.
As for you and Rounders and Shakes in Love - it's clear to me that you're just anti-American. :D